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Synthesis of New Fused Pyrano[4,3-b]pyridines from Ethyl 3-Aminopyrano[4,3-b]thieno[3,2-e]pyridine-2-carboxylate

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Abstract

Methods have been developed for the synthesis of novel fused pyrano[4,3-b]pyridine derivatives from ethyl 3-amino-4-(furan-2-yl)-7,7-dimethyl-7,8-dihydro-5H-pyrano[4,3-b]thieno[3,2-e]pyridine-2-carbox­ylate. Reactions of its 3-(phenoxycarbonyl)amino derivative with primary and secondary amines have been studied. The reactions with primary amine were accompanied by cyclization with the formation of fused pyrimidines. In the reactions with secondary amines, the product structure depended on the conditions. The synthesized compounds showed a weak antibacterial activity.

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REFERENCES

  1. McBrien, K.D., Gao, Q., Huang, S., Klohr, S.E., Wang, R.R., Pirnik, D.M., Neddermann, K.M., Bursuker, I., Kadow, K.F., and Leet, J.E., J. Nat. Prod., 1996, vol. 59, p. 1151. https://doi.org/10.1021/np960521t

    Article  CAS  PubMed  Google Scholar 

  2. Di Liberto, M.G., Caldo, A.J., Quiroga, A.D., Riveira, M.J., and Derita, M.G., ACS Omega, 2020, vol. 5, p. 7481. https://doi.org/10.1021/acsomega.0c00225

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Upadhyay, K.D., Dodia, N.M., Khunt, R.C., Chaniara, R.S., and Shah, A.K., ACS Med. Chem. Lett., 2018, vol. 9, p. 283. https://doi.org/10.1021/acsmedchemlett.7b00545

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Nguyen, S.T., Kwasny, S.M., Ding, X., Cardinale, S.C., McCarthy, C.T., Kim, H.-S., Nikaido, H., Peet, N.P., Williams, J.D., Bowlin, T.L., and Opperman, T.J., Bioorg. Med. Chem., 2015, vol. 23, p. 2024. https://doi.org/10.1016/j.bmc.2015.03.016

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Pham, H.-T., Martin, J.P., and Le, T.-G., Synth. Commun., 2020, vol. 50, p. 1845. https://doi.org/10.1080/00397911.2020.175771

    Article  CAS  Google Scholar 

  6. Paronikyan, E.G., Petrou, A., Fesatidou, M., Geroni­kaki, A., Dashyan, Sh.Sh., Mamyan, S.S., Paroni­kyan, R.G., Nazaryan, I.M., and Hakopyan, H.H., MedChemComm, 2019, vol. 10, p. 1399. https://doi.org/10.1039/c9md00187e

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Dabaeva, V.V., Pilosyan, S.G., Noravyan, A.S., Bagda­saryan, M.R., Grigoryan, G.Kh., and Aleksanyan, R.A., Pharm. Chem. J., 2008, vol. 42, p. 668. https://doi.org/10.1007/s11094-009-0218-y

    Article  CAS  Google Scholar 

  8. Dabaeva, V.V., Bagdasaryan, M.R., Noravyan, A.S., Kazaryan, Zh.V., Dzhagatspanyan, I.A., Nazaryan, I.M., and Akopyan, A.G., Pharm. Chem. J., 2016, vol. 42, p. 830. https://doi.org/10.1007/s11094-016-1381-6

    Article  CAS  Google Scholar 

  9. Dabaeva, V.V., Bagdasaryan, M.R., Dashyan, Sh.Sh., Nazaryan, I.M., Akopyan, A.G., and Paronikyan, R.G., Pharm. Chem. J., 2018, vol. 52, p. 844. https://doi.org/10.1007/s11094-019-1912-z

    Article  CAS  Google Scholar 

  10. Dabaeva, V.V., Bagdasaryan, M.R., Paronikyan, E.G., Tamazyan, R.A., Ayvazyan, A.G., and Dashyan, Sh.Sh., Russ. J. Gen. Chem., 2019, vol. 89, p. 2364. https://doi.org/10.1134/S1070363219060124

    Article  CAS  Google Scholar 

  11. Rukovodstvo po provedeniyu doklinicheskikh issledo­vanii lekarstvennykh sredstv (A Guide to Preclinical Trials of Medicines), Mironov, A.N., Ed., Moscow: Meditsina, 2012, vol. 1.

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Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 0014, Yerevan, Armenia

    V. V. Dabayeva, M. R. Baghdasaryan, E. G. Paronikyan, I. M. Barkhudaryants, H. A. Panosyan, H. M. Stepanyan & Sh. Sh. Dashyan

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  1. V. V. Dabayeva
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  2. M. R. Baghdasaryan
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  3. E. G. Paronikyan
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  7. Sh. Sh. Dashyan
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Correspondence to V. V. Dabayeva.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 1, pp. 119–127 https://doi.org/10.31857/S051474922301010X.

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Dabayeva, V.V., Baghdasaryan, M.R., Paronikyan, E.G. et al. Synthesis of New Fused Pyrano[4,3-b]pyridines from Ethyl 3-Aminopyrano[4,3-b]thieno[3,2-e]pyridine-2-carboxylate. Russ J Org Chem 59, 78–84 (2023). https://doi.org/10.1134/S1070428023010086

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